The Sexual Misadventures of the Socially Inept
by AneurysmIncoming
Summary: Sai takes his first foray into the world of Sex Education. It goes about as well as you would expect.


**Disclaimer:** **I own nothing. It all belongs to Misashi Kishimoto**

* * *

Sai had been awaiting this moment with something akin to dread.

He stared at them. They stared back.

He had to teach them about _sex_.

The other Jonin had explained that this was a meaningful team building exercise. It was meant to teach Jonin Leaders how to deal with potentially sensitive topics and a valuable way to solidify their bonds with their students. Initially, Sai had accepted the reasoning at face-value.

It had been Naruto, of all people, who'd helped him see beneath the underneath.

* * *

They'd met for lunch. Sai had come to Naruto, looking for some advice on how to approach the issue. The Hokage had instructed him to handle the issue with at least some delicacy and tact. Who better to go to than Naruto? The man himself.

The one who had taught him the importance of bonds.

However, Naruto had looked at him, his face blank, and burst into loud laughter. "Oh, man. That's great. So the others have finally gotten around to hazing you, huh?"

Sai tilted his head in confusion.

Naruto noted the look and explained further. "Uh, well... aren't they're supposed to teach the brats at the academy about uh...well, you know?"

Sai shrugged. Naruto made a great show of peering around the stand, as if he expected that even the stools might be hiding someone or something attempting to eavesdrop. Sai approved. Even in times of peace, one could never be too careful. This must be of the utmost importance. Naruto would never act this paranoid over something so trivial. He would make a fine Hokage.

Satisfied that no-one was listening, Naruto turned to face him. Sweat lined his forehead. His hands shook. Eyes darting around, he cupped his mouth and whispered "Well, you know…?"

Frantically, Naruto started miming a gesture. He formed a circle with his thumb and pointer finger with his right hand, and the pointer on his left snaked its way through the center, in and out.

Sai continued to stare at him, completely baffled. He had never seen a hand-sign like this during his time in ANBU. There was a moment of silence, as Sai attempted to interpret the cryptic gesture. Without warning Naruto stopped, his shoulders slumping in what looked like...defeat? It reminded him of a picture from one of his books. It was a portrait of a man who had lost the last shred of hope that he hadn't known he had.

Sai hoped that he wasn't the cause of the blond's mood swing. He hadn't meant to remind 'Dickless' of his sexual inadequacy. It was impolite of him. He knew that any girl that the blonde decided to copulate with would appreciate him for his personality and heart.

Perhaps his friend needed a reminder of this? Sai was about to comfort the blond but he was interrupted by Naruto snapping his head up, looking directly in his eyes. The blonde had made a quick recovery. His eyes lit up with mirth."You know what? I'm not the best the guy to talk to about this. There's isn't much I can do on my own and I'm sure you have a lot to learn. You need an expert."

The blonde rubbed his chin in thought. "Hey, I know! Maybe you can ask Ino. She knows how to get around and I'm sure she'd have all kinds of good advice."

Before Sai could respond, Naruto spun around, practically jumping from his seat. As he ran down the street, Naruto looked over his shoulder to shout at him "Anyways, good luck. Let me know how it turns out!"

Sai could hear the blond's cackles as he ran off into the distance.

* * *

Sai could recall everything that led him to this moment with perfect clarity.

He was certain that only seconds had passed yet it felt like an eternity. His students were starting to look impatient and a little disconcerted. Sai knew he had to say something, _anything_. He could not fail his students. Not at this juncture. It was his duty as their teacher.

Yet he couldn't figure out where to begin.

Perhaps if the encounter with Ino had gone better, he wouldn't have found himself in this position.

* * *

He couldn't help but keep a wary eye on Ino. Her left eye had developed an erratic twitch. She appeared to be breaking out in a cold sweat, her lips locked in a rictus grin. Had he done something to offend her?

Sakura had berated him, many a time, for his lack of a filter. That had only served to confuse him. How would a rebreather mask help in any social situation? Sakura could be silly at times. Sai smiled at the thought and shook his head, feeling a strange sense of camaraderie with her; he wasn't the only one who failed to grasp the finer details of social interaction.

Finally, he caught onto his social gaffe.

Ah, yes. He forgot to ask about her day!

He didn't have to do this with Naruto, Kakashi or Sakura, but they were among his closest friends and Ino was merely an acquaintance. So he still had to observe certain niceties with her.

"How are you?" he asked with a pleasant smile. It fell slightly when there was no shift in her demeanour. "I didn't mean any offense. Naruto said that you know how to get around and that you were an expert on these matters. I still have much to learn about sexual intercourse. He tried his best, but he said that he was only one man and that no one could fill a hole that big."

Silence.

Sai brought out his handbook. He had never gotten a reaction that was even remotely similar to this and he needed a point of reference. He flipped through the pages, desperate to find some explanation for the girl's behavior. He just couldn't understand what he'd done wrong.

Ino's eye twitched with increased frequency, her legs turning inwards. The expression she wore cold, clinical. Despite this, her mouth stretched outwards, locked in a manic grin. Sai felt her gaze pierce into him.

He wasn't sure why but he was forcefully reminded of the way Orochimaru would eye Sasuke when he thought that the Uchiha wasn't looking. Sai had to repress a shudder.

He felt disturbed.

"I think...I'm going to leave."

The office was silent save for the creak of a closing door.

* * *

Sai's Genin were shifting uncomfortably before him.

He'd always been surprised by how generic the three girls looked.

The silence between them stretched.

Finally, he had an epiphany. While the rest of his attempts to gather information had been a complete failure, his conversation with the Rokudaime had been illuminating. Sai knew exactly where to begin.

Breaking the silence between them, Sai began his lecture.

* * *

The Rokudaime stared at Sai in contemplation.

After his last failure, Sai had become desperate. Naruto had failed him, Ino had failed him and Sai, having been made painfully aware of her disposition towards discussing sex, had opted not to go Sakura for help.

There had been only one option: Kakashi.

If anything he should have come to him first.

Surely, someone so dedicated to studies on the topic of sex should be a font of knowledge.

As he waited for Kakashi reply, Sai wondered if this was what the first disciple of the Sage had felt like. He, the pupil eager to imbibe the wisdom his teacher was about to impart and Kakashi, the wise sage who spent his days contemplating the answer to the ultimate questions, studying in the form of little orange books, waiting to share his knowledge with one he deemed worthy.

Kakashi appeared to draw himself out of his reverie and spoke. "Mah, you have such a serious look on your face, Sai. This isn't a big deal. It's only sex."

Sai believed that this was the Rokudaime's attempt at a joke. Believing otherwise would mean a spit in the face of everything he believed in.

Taking his lack of a response as agreement, Kakashi moved on. "Well, sex...means a lot of things to different people.

That much, at least, Sai had figured out on his own. Contemplating what it meant to Ino made him want to break out in a cold sweat. He pushed that thought aside. There was only so much stress he could deal with in a day.

Kakashi rubbed the back of head, looking a little sheepish and he said, "The reason why you've had so much trouble today is because...sex is somewhat of a social taboo so a lot of people tend to react negatively when you bring it up but you shouldn't let that discourage you. These things are important to talk about, sex education is important and quite frankly, my cute little students have always been prudes."

Sai made a mental note to look up what the word 'taboo' meant later. He had a lecture to receive. If everything went well, one to give to his students later as well.

The Rokudaime continued. "For a lot of people, sex is a means of expressing love for one another. Much like when Toshi saved Ayami saved from Coolness McDark in Icha Icha - Grit. However, Toshi knew that he would never reciprocate her feelings in the same way. His heart belonged to another. That didn't stop him. He lay with her, dick in hand and a grin on his face, and plowed her into next week. Toshi was a man who knew how to compartmentalize."

Sai wasn't certain what Kakashi was getting at but he nodded his head sagely.

Kakashi was giggling and his cheeks were tinged red. Encouraged by his audience' interest, the Hokage carried on. "Perhaps Toshi is not the best example of that. Once he had settled down with his true lady love, Ayami found him and demanded he pay child support and he spent the rest of his days caught between two harridans and poor. Truly, a cautionary tale for us all."

This at least, Sai understood perfectly. One should never get himself caught between multiple commitments after all. It was just common sense.

The Hokage ruefully shook his head. "You see Sai, sex is a very complicated subject that one can spend lifetimes learning the various intricacies and subtle meanings it can convey. There's many ways to learn, the Icha Icha series being a thesis on sexual dynamics. Or if you prefer the more hands on approach, you can always just hire a prostitute! Do you see what I'm getting at?"

Kakashi handed him a book. On the cover were a man and a woman, entwined in a way that he would never had thought possible until he had met Orochimaru.

Sai understood perfectly.

* * *

"Sex is something that you must never talk about even if it's important to."

His Genin eye's grew wide, a vision of dawning terror. They traded looks with one another. Sai could also see hints of disconcertion there too as he stared at them. He had their attention at least. Things were already going better than he had hoped.

He resumed his speech. "Also, it is something that happens between two people who love each other and sometimes when they don't if one partner has enough money. Also, it never happens for free?"

Sai was still a bit unsure about that, but Kakashi had been particularly emphatic on that point.

Sai reached into his pocket, and pulled out the book he gotten from the Hokage. The cover was emblazoned with the title, "Icha Icha - A Beginner's Guide"

He showed the book to his students. They all took a few steps forward, squinting to get a better look. If anything they're eyes grew wider, their terror reaching new heights.

Sai's favorite student, Shiho, finally broke the student's silence. "Um, Sensei...you do know that sex education is a required class at the academy, right?"

Sai frowned at her, his face a picture of consternation. "I was lead to believe that we were required to instruct our Genin on the finer points of sex. Why would the other Jonin have told me that if you wasn't true?"

A small frown played on the Jonin's face for a moment, but it was his least favorite student, Taki, that answered him. She shrugged. "Maybe they were just playing a prank on you?"

Sai considered this for a moment. He would never expect that his fellow teachers would act in such an unprofessional manner but there was something that kept nagging at him.

 _"So the other Jonin finally got around to hazing you, huh?"_

Sai smacked his fist against his hand in realization. It was Naruto.

Sai had forgotten to thank him for his help earlier. The Jonin couldn't help but feel a little upset with himself. Even with his closest friends he still wasn't able exercise correct social protocol. This epiphany wasn't any help with his current situation, unfortunately. He would make it up to the blond. Perhaps he could get him some kind of sexual aid to help him with his performance problems.

Shaking his head, Sai addressed his students. "But then what was the point of all this? I thought I knew everything but now I feel like I know less than I ever had before."

The student he had no opinion of one way or the other, Shion, blushed. She poked her fingers together, determinedly not making eye contact with anyone. She stammered, "W-w-well, we could teach you what we know, Sensei?"

The other two girls looked at Shion with confusion. The looks changed to ones of understanding and they nodded to each other. Taki looked at him, a grin on her face and a leer in her eye. "Shion's right, Sensei. If there's anything you need, and I mean _anything_ , we'd all be happy to help."

Sai looked at the three girls and merely raised a single brow.

* * *

This emotion was one that Sai still wasn't familiar with.

Excitement.

Taki had an arm draped over his shoulder. Sai had never thought that his venture would have resulted in this. Having sex demonstrated to him couldn't be compared to what he learned during his tenure at ROOT. This was the crowning moment of his life.

"I didn't know that was physically possible..." Sai's eyes were alight with an almost child-like glee.

Shiho sighed. "Sensei, you're reading the book upside-down."

Sai blinked, "Oh, that makes more sense."

They all sat on the roof of the academy. His students were gathered around him, attempting to explain the finer points of the book to him. Honestly, he had never thought that sex could be this complex a subject. The myriad of social connotations and creative ways that one could perform the act itself.

It was a bit overwhelming.

He'd always considered sex as nothing more than a functional practice. One piece of anatomy entering another, wait nine months and you have another willing soldier to teach the virtues of the Will of Fire. Thanks to the help from his students, he understood a bit better now.

Sai reflected that while his ordeal had largely been an exercise in futility, he had succeeded in at least on thing.

His bond with his students was tighter than it had ever been before.


End file.
